Triethylamine → Benzyl prop-2-yn-1-ylcarbamate

HRID 49565Notes

Reaction equation

HRID 49565 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].C(N(CC)CC)C.[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCC)(=O)C>[C:20]([NH:4][CH2:1][C:2]#[CH:3])([O:19][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 239041Propargylamine

Product 1

HCID 11137906Benzyl prop-2-yn-1-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of propargylamine (20 g) and triethylamine (60.7 mL) in ethyl acetate (500 mL) was added benzyloxycarbonyl chloride (71.7 g) slowly while maintaining the reaction temperature between −5° C. and +5° C. The mixture was then stirred at room temperature overnight. The mixture was washed sequentially with 1.5 M HCl (200 mL), 5% NaHCO3 in water (200 mL), and saturated aqueous sodium chloride (100 mL). The solvent was switched to hexane while the desired product precipitated as colorless crystals (60.1 g).

Workup

  1. temperaturewhile maintaining the reaction temperature between −5° C. and +5° C
  2. washThe mixture was washed sequentially with 1.5 M HCl (200 mL), 5% NaHCO3 in water (200 mL), and saturated aqueous sodium chloride (100 mL)
  3. customprecipitated as colorless crystals (60.1 g)

Sources & evidence

ORD record
ord-528fffcb5f3048898cfbab694e12c1e8
Source dataset
uspto-grants-2004_03
Patent number
US06706885B2

Reaction notes

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